US8241762B2 - Charge transport materials for luminescent applications - Google Patents
Charge transport materials for luminescent applications Download PDFInfo
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- US8241762B2 US8241762B2 US12/129,785 US12978508A US8241762B2 US 8241762 B2 US8241762 B2 US 8241762B2 US 12978508 A US12978508 A US 12978508A US 8241762 B2 US8241762 B2 US 8241762B2
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- charge transport
- binaphthyl
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- 239000000463 material Substances 0.000 title claims description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000005577 anthracene group Chemical group 0.000 claims abstract description 6
- 125000005647 linker group Chemical group 0.000 claims abstract description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 6
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 98
- -1 —N(R7)(R8) Chemical group 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
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- 239000000047 product Substances 0.000 description 10
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- 238000003756 stirring Methods 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 229910052782 aluminium Inorganic materials 0.000 description 3
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- 238000005401 electroluminescence Methods 0.000 description 3
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
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- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
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- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
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- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical class C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 2
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 2
- IBFNLCZFNABMHC-UHFFFAOYSA-N 9-(4-methylnaphthalen-1-yl)anthracene Chemical compound C12=CC=CC=C2C(C)=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 IBFNLCZFNABMHC-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 2
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
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- KBXXZTIBAVBLPP-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-(4-methylphenyl)methyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(C)C=C1 KBXXZTIBAVBLPP-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 description 1
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Images
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- This disclosure relates in general to materials that can be used as hosts for light-emitting materials in luminescent applications.
- the disclosure further relates to electronic devices having at least one active layer comprising such a host material.
- organic photoactive electronic devices such as organic light emitting diodes (“OLED”), that make up OLED displays
- OLED organic light emitting diodes
- the organic active layer is sandwiched between two electrical contact layers in an OLED display.
- the organic photoactive layer emits light through the light-transmitting electrical contact layer upon application of a voltage across the electrical contact layers.
- organic electroluminescent compounds As the active component in light-emitting diodes. Simple organic molecules, conjugated polymers, and organometallic complexes have been used.
- Devices that use photoactive materials frequently include one or more charge transport layers, which are positioned between a photoactive (e.g., light-emitting) layer and a contact layer (hole-injecting contact layer).
- a device can contain two or more contact layers.
- a hole transport layer can be positioned between the photoactive layer and the hole-injecting contact layer.
- the hole-injecting contact layer may also be called the anode.
- An electron transport layer can be positioned between the photoactive layer and the electron-injecting contact layer.
- the electron-injecting contact layer may also be called the cathode.
- Charge transport materials can also be used as hosts in combination with the photoactive materials.
- T is a charge transport moiety having the formula —Ar 1 -An-Ar 2 and LG is a linking group
- an electronic device comprising at least one layer comprising the above compound.
- FIG. 1 includes an illustration of one example of an organic electronic device.
- adjacent to when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer.
- alkyl is intended to mean a group derived from an aliphatic hydrocarbon having one point of attachment, and includes a linear, a branched, or a cyclic group. The term is intended to include heteroalkyls.
- alkylene is intended to mean a group derived from an aliphatic hydrocarbon and having two or more points of attachment. In some embodiments, an alkyl group has from 1-20 carbon atoms.
- aryl is intended to mean a group derived from an aromatic hydrocarbon having one point of attachment.
- the term is intended to include heteroaryls.
- arylene is intended to mean a group derived from an aromatic hydrocarbon having two points of attachment. In some embodiments, an aryl group has from 3-60 carbon atoms.
- binaphthyl is intended to mean a group having two naphthalene units joined by a single bond.
- the binaphthyl group is 1,1-binaphthyl, which is attached at the 3-, 4-, or 5-position; in some embodiments, 1,2-binaphthyl, which is attached at the 3-, 4-, or 5-position on the 1-naphthyl moiety, or the 4- or 5-position on the 2-naphthyl moiety; and in some embodiments, 2,2-binaphthyl, which is attached at the 4- or 5-position.
- blue refers to radiation that has an emission maximum at a wavelength in a range of approximately 400-500 nm.
- charge transport when referring to a layer, material, member, or structure is intended to mean such layer, material, member, or structure facilitates migration of such charge through the thickness of such layer, material, member, or structure with relative efficiency and small loss of charge.
- Hole transport materials facilitate positive charge; electron transport material facilitate negative charge.
- light-emitting materials may also have some charge transport properties, the term “charge transport layer, material, member, or structure” is not intended to include a layer, material, member, or structure whose primary function is light emission.
- fluoro indicates that one or more hydrogen atoms have been replaced with a fluorine atom.
- hetero indicates that one or more carbon atoms have been replaced with a different atom.
- the different atom is N, O, or S.
- layer is used interchangeably with the term “film” and refers to a coating covering a desired area.
- the term is not limited by size.
- the area can be as large as an entire device or as small as a specific functional area such as the actual visual display, or as small as a single sub-pixel.
- Layers and films can be formed by any conventional deposition technique, including vapor deposition, liquid deposition (continuous and discontinuous techniques), and thermal transfer.
- Continuous deposition techniques include but are not limited to, spin coating, gravure coating, curtain coating, dip coating, slot-die coating, spray coating, and continuous nozzle coating.
- Discontinuous deposition techniques include, but are not limited to, ink jet printing, gravure printing, and screen printing.
- organic electronic device or sometimes just “electronic device,” is intended to mean a device including one or more organic semiconductor layers or materials.
- substituents include alkyl, aryl, nitro, cyano, —N(R 7 )(R 8 ), halo, hydroxy, carboxy, alkenyl, alkynyl, cycloalkyl, heteroaryl, alkoxy, aryloxy, heteroaryloxy, alkoxycarbonyl, perfluoroalkyl, perfluoroalkoxy, arylalkyl, thioalkoxy, —S(O) 2 —N(R′)(R′′), —C( ⁇ O)—N(R′)(R′′), (R′)(R′′)N-alkyl, (R′)(R′′)N-alkoxyalkyl, (R′)(R′′)N-alkoxyalkyl, (R′)(R′′)N-alkoxyalkyl, (R′)(R′′)N-alkoxyalkyl, (R′)(R′′)N-alkoxyalkyl, (R′)(
- photoactive is intended to mean to any material that exhibits electroluminescence or photosensitivity.
- the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
- a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
- “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
- the new compounds described herein are particularly useful as host materials for photoactive materials.
- the compounds have the formula T-LG-T, where T is a charge transport moiety and LG is a linking group.
- the charge transport moiety has the formula —Ar 1 -An-Ar 2
- An is an anthracene attached at the 9- and 10-positions.
- the anthracene moiety has at least one substituent.
- the substituent is selected from the group consisting of C1-12 alkyl and C1-12 alkoxy.
- the anthracene is substituted at the 2- and 6-position.
- the charge transport moiety T is selected from groups A-G below.
- LG has Formula II:
- LG is 1,4-phenylene.
- LG is a binaphthylene group.
- the binapthylene group has at least one substituent selected from the group consisting of C1-12 alkyl and C1-12 alkoxy.
- LG has Formula III:
- R1 and R2 are the same or different and are C1-1 2 alkyl groups. In some embodiments, R1 and R2 are C6-10 groups.
- the new charge transport compound is Compound H1 through H5 below.
- the new charge transport compounds can be prepared by known coupling and substitution reactions.
- An exemplary preparation is given in the Examples.
- the new compounds described herein can be formed into films using liquid deposition techniques.
- the present invention also relates to an electronic device comprising at least one photoactive layer positioned between two electrical contact layers, wherein the at least one layer of the device includes the new charge transport compound described herein.
- Organic electronic devices that may benefit from having one or more layers comprising the new charge transport materials described herein include, but are not limited to, (1) devices that convert electrical energy into radiation (e.g., a light-emitting diode, light emitting diode display, or diode laser), (2) devices that detect signals through electronics processes (e.g., photodetectors, photoconductive cells, photoresistors, photoswitches, phototransistors, phototubes, IR detectors), (3) devices that convert radiation into electrical energy, (e.g., a photovoltaic device or solar cell), and (4) devices that include one or more electronic components that include one or more organic semi-conductor layers (e.g., a transistor or diode).
- devices that convert electrical energy into radiation e.g., a light-emitting diode, light emitting diode display, or diode laser
- devices that detect signals through electronics processes e.g., photodetectors, photoconductive cells, photoresistors, photoswitches, phototrans
- the device 100 has a first electrical contact layer, an anode layer 110 and a second electrical contact layer, a cathode layer 160 , and a photoactive layer 140 between them.
- Adjacent to the anode is a buffer layer 120 .
- Adjacent to the buffer layer is a hole transport layer 130 , comprising hole transport material.
- Adjacent to the cathode may be an electron transport layer 150 , comprising an electron transport material.
- devices may use one or more additional hole injection or hole transport layers (not shown) next to the anode 110 and/or one or more additional electron injection or electron transport layers (not shown) next to the cathode 160 .
- Layers 120 through 150 are individually and collectively referred to as the active layers.
- the different layers have the following range of thicknesses: anode 110 , 500-5000 ⁇ , in one embodiment 1000-2000 ⁇ ; buffer layer 120 , 50-2000 ⁇ , in one embodiment 200-1000 ⁇ ; hole transport layer 130 , 50-2000 ⁇ , in one embodiment 200-1000 ⁇ ; photoactive layer 140 , 10-2000 ⁇ , in one embodiment 100-1000 ⁇ ; layer 150 , 50-2000 ⁇ , in one embodiment 100-1000 ⁇ ; cathode 160 , 200-10000 ⁇ , in one embodiment 300-5000 ⁇ .
- the location of the electron-hole recombination zone in the device, and thus the emission spectrum of the device can be affected by the relative thickness of each layer.
- the desired ratio of layer thicknesses will depend on the exact nature of the materials used.
- the photoactive layer 140 can be a light-emitting layer that is activated by an applied voltage (such as in a light-emitting diode or light-emitting electrochemical cell), or a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage (such as in a photodetector).
- an applied voltage such as in a light-emitting diode or light-emitting electrochemical cell
- a layer of material that responds to radiant energy and generates a signal with or without an applied bias voltage
- Examples of photodetectors include photoconductive cells, photoresistors, photoswitches, phototransistors, and phototubes, and photovoltaic cells, as these terms are described in Markus, John, Electronics and Nucleonics Dictionary, 470 and 476 (McGraw-Hill, Inc. 1966).
- the charge transport compounds described herein can be present in the photoactive layer or in a charge transport layer.
- the charge transport compounds described herein are useful as hosts for the photoactive materials in layer 140 .
- the photoactive material can be any electroluminescent (“EL”) material having the desired color.
- Electroluminescent materials include small molecule organic fluorescent compounds, fluorescent and phosphorescent metal complexes, conjugated polymers, and mixtures thereof. Examples of fluorescent compounds include, but are not limited to, pyrene, perylene, rubrene, coumarin, derivatives thereof, and mixtures thereof.
- metal complexes include, but are not limited to, metal chelated oxinoid compounds, such as tris(8-hydroxyquinolato)aluminum (Alq3); cyclometalated iridium and platinum electroluminescent compounds, such as complexes of iridium with phenylpyridine, phenylquinoline, or phenylpyrimidine ligands as disclosed in Petrov et al., U.S. Pat. No. 6,670,645 and Published PCT Applications WO 03/063555 and WO 2004/016710, and organometallic complexes described in, for example, Published PCT Applications WO 03/008424, WO 03/091688, and WO 03/040257, and mixtures thereof.
- metal chelated oxinoid compounds such as tris(8-hydroxyquinolato)aluminum (Alq3)
- cyclometalated iridium and platinum electroluminescent compounds such as complexes of iridium with pheny
- Electroluminescent emissive layers comprising a charge carrying host material and a metal complex have been described by Thompson et al., in U.S. Pat. No. 6,303,238, and by Burrows and Thompson in published PCT applications WO 00/70655 and WO 01/41512.
- conjugated polymers include, but are not limited to poly(phenylenevinylenes), polyfluorenes, poly(spirobifluorenes), polythiophenes, poly(p-phenylenes), copolymers thereof, and mixtures thereof.
- the EL material is a cyclometalated complex of iridium.
- the complex has two ligands selected from phenylpyridines, phenylquinolines, and phenylisoquinolines, and a third ligand with is a ⁇ -dienolate.
- the ligands may be unsubstituted or substituted with F, D, alkyl, CN, or aryl groups.
- the EL material is selected from the group consisting of a non-polymeric spirobifluorene compound and a fluoranthene compound.
- the EL material is a compound having aryl amine groups. In one embodiment, the EL material is selected from the formulae below:
- A is the same or different at each occurrence and is an aromatic group having from 3-60 carbon atoms;
- Q is a single bond or an aromatic group having from 3-60 carbon atoms
- n and m are independently an integer from 1-6.
- At least one of A and Q in each formula has at least three condensed rings.
- m and n are equal to 1.
- Q is a styryl or styrylphenyl group.
- Q is an aromatic group having at least two condensed rings.
- Q is selected from the group consisting of naphthalene, anthracene, chrysene, pyrene, tetracene, xanthene, perylene, coumarin, rhodamine, quinacridone, and rubrene.
- A is selected from the group consisting of phenyl, tolyl, naphthyl, and anthracenyl groups.
- the EL material has the formula below:
- Y is the same or different at each occurrence and is an aromatic group having 3-60 carbon atoms
- Q′ is an aromatic group, a divalent triphenylamine residue group, or a single bond.
- the EL material is an aryl acene. In some embodiments, the EL material is a non-symmetrical aryl acene. In some embodiments, the EL material is a chrysene derivative. The term “chrysene” is intended to mean 1,2-benzophenanthrene. In some embodiments, the EL material is a chrysene having aryl substituents. In some embodiments, the EL material is a chrysene having arylamino substituents. In some embodiments, the EL material is a chrysene having two different arylamino substituents.
- the EL material has blue or green emission.
- the ratio of host material to EL material is in the range of 5:1 to 20:1; in some embodiments, 10:1 to 15:1.
- the new charge transport compounds described herein are particularly useful as hosts for fluorescent organic compounds, including aromatic and arylamino-aromatic compounds.
- the other layers in the device can be made of any materials that are known to be useful in such layers.
- the anode 110 is an electrode that is particularly efficient for injecting positive charge carriers. It can be made of, for example, materials containing a metal, mixed metal, alloy, metal oxide or mixed-metal oxide, or it can be a conducting polymer, or mixtures thereof. Suitable metals include the Group 11 metals, the metals in Groups 4-6, and the Group 8-10 transition metals. If the anode is to be light-transmitting, mixed-metal oxides of Groups 12, 13 and 14 metals, such as indium-tin-oxide, are generally used.
- the anode 110 can also comprise an organic material such as polyaniline as described in “Flexible light-emitting diodes made from soluble conducting polymer,” Nature vol. 357, pp 477-479 (11 Jun. 1992). At least one of the anode and cathode is desirably at least partially transparent to allow the generated light to be observed.
- the buffer layer 120 comprises buffer material and may have one or more functions in an organic electronic device, including but not limited to, planarization of the underlying layer, charge transport and/or charge injection properties, scavenging of impurities such as oxygen or metal ions, and other aspects to facilitate or to improve the performance of the organic electronic device.
- Buffer materials may be polymers, oligomers, or small molecules. They may be vapour deposited or deposited from liquids which may be in the form of solutions, dispersions, suspensions, emulsions, colloidal mixtures, or other compositions.
- the buffer layer can be formed with polymeric materials, such as polyaniline (PANI) or polyethylenedioxythiophene (PEDOT), which are often doped with protonic acids.
- the protonic acids can be, for example, poly(styrenesulfonic acid), poly(2-acrylamido-2-methyl-1-propanesulfonic acid), and the like.
- the buffer layer can comprise charge transfer compounds, and the like, such as copper phthalocyanine and the tetrathiafulvalene-tetracyanoquinodimethane system (TTF-TCNQ).
- charge transfer compounds such as copper phthalocyanine and the tetrathiafulvalene-tetracyanoquinodimethane system (TTF-TCNQ).
- the buffer layer comprises at least one electrically conductive polymer and at least one fluorinated acid polymer.
- electrically conductive polymer and at least one fluorinated acid polymer.
- hole transport materials for layer 130 have been summarized for example, in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition, Vol. 18, p. 837-860, 1996, by Y. Wang. Both hole transporting molecules and polymers can be used. Commonly used hole transporting molecules are: N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine (TPD), 1,1-bis[(di-4-tolylamino) phenyl]cyclohexane (TAPC), N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]-4,4′-diamine (ETPD), tetrakis-(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine (PDA), a-
- hole transporting polymers are polyvinylcarbazole, (phenylmethyl)-polysilane, and polyaniline. It is also possible to obtain hole transporting polymers by doping hole transporting molecules such as those mentioned above into polymers such as polystyrene and polycarbonate. In some cases, a polymer of triarylamine is used, particularly a copolymer of triarylamine and fluorene. In some cases the polymer or copolymer is crosslinkable.
- additional electron transport materials which can be used in layer 150 include metal chelated oxinoid compounds, such as tris(8-hydroxyquinolato)aluminum (Alq 3 ); bis(2-methyl-8-quinolinolato)(para-phenyl-phenolato)aluminum(III) (BAIQ); and azole compounds such as 2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD) and 3-(4-biphenylyl)-4-phenyl-5-(4-t-butylphenyl)-1,2,4-triazole (TAZ), and 1,3,5-tri(phenyl-2-benzimidazole)benzene (TPBI); quinoxaline derivatives such as 2,3-bis(4-fluorophenyl)quinoxaline; phenanthroline derivatives such as 9,10-diphenylphenanthroline (DPA) and 2,9-dimethyl-4
- the cathode 160 is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
- the cathode can be any metal or nonmetal having a lower work function than the anode.
- Materials for the cathode can be selected from alkali metals of Group 1 (e.g., Li, Cs), the Group 2 (alkaline earth) metals, the Group 12 metals, including the rare earth elements and lanthanides, and the actinides. Materials such as aluminum, indium, calcium, barium, samarium and magnesium, as well as combinations, can be used.
- Li-containing organometallic compounds, LiF, and Li 2 O can also be deposited between the organic layer and the cathode layer to lower the operating voltage.
- anode 110 there can be a layer (not shown) between the anode 110 and buffer layer 120 to control the amount of positive charge injected and/or to provide band-gap matching of the layers, or to function as a protective layer.
- Layers that are known in the art can be used, such as copper phthalocyanine, silicon oxy-nitride, fluorocarbons, silanes, or an ultra-thin layer of a metal, such as Pt.
- some or all of anode layer 110 , active layers 120 , 130 , 140 , and 150 , or cathode layer 160 can be surface-treated to increase charge carrier transport efficiency.
- the choice of materials for each of the component layers is preferably determined by balancing the positive and negative charges in the emitter layer to provide a device with high electroluminescence efficiency.
- each functional layer can be made up of more than one layer.
- the device can be prepared by a variety of techniques, including sequential vapor deposition of the individual layers on a suitable substrate.
- Substrates such as glass, plastics, and metals can be used.
- Conventional vapor deposition techniques can be used, such as thermal evaporation, chemical vapor deposition, and the like.
- the organic layers can be applied from solutions or dispersions in suitable solvents, using conventional coating or printing techniques, including but not limited to spin-coating, dip-coating, roll-to-roll techniques, ink-jet printing, screen-printing, gravure printing and the like.
- the new charge transport compounds described herein are particularly suited to liquid deposition processes for forming films.
- the efficiency of devices made with the chrysene compounds described herein can be further improved by optimizing the other layers in the device.
- more efficient cathodes such as Ca, Ba or LiF can be used.
- Shaped substrates and novel hole transport materials that result in a reduction in operating voltage or increase quantum efficiency are also applicable.
- Additional layers can also be added to tailor the energy levels of the various layers and facilitate electroluminescence.
- This example illustrates the preparation of Compound H5, 10,10′-(6,6′-(4,4′-(perfluoropropane-2,2-diyl)bis(4,1-phenylene))bis(naphthalene-6,2-diyl))bis(9-(4-methylnaphthalen-1-yl)anthracene).
- Relative Amount Amount MW Equiva- Compound (g) (mmol) (g/mol) lents 6,6′-(4,4′-(perfluoropropane- 1.70 2.00 852.66 1.00 2,2-diyl)bis(4,1-phenylene))bis (naphthalene-6,2-diyl) bis(trifluoromethanesulfonate) 4,4,5,5-tetramethyl-2-(10-(4- 1.81 4.20 430.35 2.10 methylnaphthalen-1- yl)anthracen-9-yl)-1,3,2- dioxaborolane Pd(dppf) 2 Cl 2 65 mg 0.08 816.63 0.04 Potassium phosphate 3.68 16.00 230.28 8.00 K 3 PO 4 •H 2 O Sodium carbonate 8.00 mL 16.00 105.99 8.00 Na 2 CO 3 (2M) THF 60 (mL) 10,10′-(6,6′-(4,4′- 2.32 3.00 1161
- the crude product was collected by filtration, washed with water then with methanol (400 mL) dried in a vacuum oven overnight. TLC analysis of the solid material indicated that all starting triflate had been consumed and the product appeared as the major spot with a bright blue color under UV light irradiation. The Rf value of the product was found similar to that of starting triflate but it was seen non-fluorescent.
- the crude product was then dissolved in toluene (150 mL) with gentle heating under nitrogen and stirred with active carbon (20 g) at ambient temperature for 2 hr. After which, the solution was filtered through a bed of Florosil* and the solvent was removed by rotary evaporation. The product was further purified by crystallization from DCM/Hexane to give the product as a white powder, yield, 1.75 g (75%) with a purity >99.9% by HPLC analysis. NMR spectra are consistent with the structures expected.
- This example illustrates the preparation of Compound H2, 10,10′-(4,4′-(2,2′-dioctyl-1,1′-binaphthyl-4,4′-diyl)bis(4,1-phenylene))bis(9-(naphthalen-2-yl)anthracene).
- Relative Amount Amount MW Equiva- Compound (g) (mmol) (g/mol) lents 4-(10-(naphthalen-2- 2.71 5.125 528.54 2.05 yl)anthracen-9-yl)phenyl trifluoromethanesulfonate 2,2′-(2,2′-dioctyl-1,1′- 1.83 2.50 730.67 1.00 binaphthyl-4,4′- diyl)bis(4,4,5,5-tetramethyl- 1,3,2-dioxaborolane) Pd(dppf) 2 Cl 2 82 mg 0.10 816.63 0.04 Potassium phosphate 4.60 20.00 230.28 8.00 K 3 PO 4 •H 2 O Sodium carbonate 10.0 mL 20.00 105.99 8.00 Na 2 CO 3 (2M) THF 80.0 (mL) 10,10′-(4,4′-(2,2′-dioctyl-1,1′ 3.09 2.50 1235.68
- HPLC analysis on the organic layer indicated that almost all binaphthyl diborate had been consumed and the product appeared as a major spot with strong blue fluorescence under UV light irradiation.
- the organic layer was diluted with toluene (100 mL) and separated. The aqueous layer was extracted with toluene (2 ⁇ 25 mL). The organic fractions were combined, washed with diluted HCl (5%, 1 ⁇ 60 mL) water (2 ⁇ 60 mL) and saturated brine (60 mL), and dried with MgSO 4 . The volume of the solution was reduced to about 8 mL on a rotavap and then added dropwise to methanol (200 mL) with stirring.
Abstract
Description
-
- An is a divalent anthracene moiety;
- Ar1 is a single bond or an aromatic group selected from the group consisting of naphthyl, binaphthyl, naphthylphenylene, naphthylbiphenylene, and naphthylbinaphthylene;
- Ar2 is an aromatic group selected from the group consisting of naphthyl, binaphthyl, naphthylphenylene, naphthylbiphenylene, and naphthylbinaphthylene; and
- LG is selected from the group consisting of biphenylene, binaphthylene, and Formula I
-
- Q1 and Q2 are the same or different and are selected from the group consisting of alkyl and aryl, or Q1 and Q2 taken together are alkylene, and
- Ar3 and Ar4 are the same or different and are selected from the group consisting of phenylene and naphthylene.
-
- An is a divalent anthracene moiety;
- Ar1 is a single bond or an aromatic group selected from the group consisting of naphthyl, binaphthyl, naphthylphenylene, naphthylbiphenylene, and naphthylbinaphthylene; and
- Ar2 is an aromatic group selected from the group consisting of naphthyl, binaphthyl, naphthylphenylene, naphthylbiphenylene, and naphthylbinaphthylene.
In the above groups, possible points of attachment to LG are shown as - - - *. The above groups may also be substituted.
-
- LG is a linking group and is selected from the group consisting of biphenylene, binaphthylene, and Formula I
-
- Q1 and Q2 are the same or different and are selected from the group consisting of alkyl and aryl, or Q1 and Q2 taken together are alkylene, and
- Ar3 and Ar4 are the same or different and are selected from the group consisting of phenylene and napthylene.
where R1 and R2 are the same or different and are C1-1 2 alkyl groups. In some embodiments, R1 and R2 are C6-10 groups.
Relative | ||||
Amount | Amount | MW | Equiva- | |
Compound | (g) | (mmol) | (g/mol) | lents |
6,6′-(4,4′-(perfluoropropane- | 1.70 | 2.00 | 852.66 | 1.00 |
2,2-diyl)bis(4,1-phenylene))bis | ||||
(naphthalene-6,2-diyl) | ||||
bis(trifluoromethanesulfonate) | ||||
4,4,5,5-tetramethyl-2-(10-(4- | 1.81 | 4.20 | 430.35 | 2.10 |
methylnaphthalen-1- | ||||
yl)anthracen-9-yl)-1,3,2- | ||||
dioxaborolane |
Pd(dppf)2Cl2 | 65 | mg | 0.08 | 816.63 | 0.04 |
Potassium phosphate | 3.68 | 16.00 | 230.28 | 8.00 |
K3PO4•H2O |
Sodium carbonate | 8.00 | mL | 16.00 | 105.99 | 8.00 |
Na2CO3 (2M) | |||||
THF | 60 | (mL) |
10,10′-(6,6′-(4,4′- | 2.32 | 3.00 | 1161.28 | |
(perfluoropropane-2,2- | (Theo- | |||
diyl)bis(4,1- | retical) | |||
phenylene))bis(naphthalene- | ||||
6,2-diyl))bis(9-(4- | ||||
methylnaphthalen-1- | ||||
yl)anthracene) | ||||
Relative | ||||
Amount | Amount | MW | Equiva- | |
Compound | (g) | (mmol) | (g/mol) | lents |
4-(10-(naphthalen-2- | 2.71 | 5.125 | 528.54 | 2.05 |
yl)anthracen-9-yl)phenyl | ||||
trifluoromethanesulfonate | ||||
2,2′-(2,2′-dioctyl-1,1′- | 1.83 | 2.50 | 730.67 | 1.00 |
binaphthyl-4,4′- | ||||
diyl)bis(4,4,5,5-tetramethyl- | ||||
1,3,2-dioxaborolane) |
Pd(dppf)2Cl2 | 82 | mg | 0.10 | 816.63 | 0.04 |
Potassium phosphate | 4.60 | 20.00 | 230.28 | 8.00 |
K3PO4•H2O |
Sodium carbonate | 10.0 | mL | 20.00 | 105.99 | 8.00 |
Na2CO3 (2M) | |||||
THF | 80.0 | (mL) |
10,10′-(4,4′-(2,2′-dioctyl-1,1′ | 3.09 | 2.50 | 1235.68 | |
binaphthyl-4,4′-diyl)bis(4,1- | (Theo- | |||
phenylene))bis(9- | retical) | |||
(naphthalen-2-yl)anthracene) | ||||
Claims (8)
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US12/129,785 US8241762B2 (en) | 2007-06-01 | 2008-05-30 | Charge transport materials for luminescent applications |
US13/547,899 US8460802B2 (en) | 2007-06-01 | 2012-07-12 | Charge transport materials for luminescent applications |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110152587A1 (en) * | 2007-04-13 | 2011-06-23 | Hyo Nim Shin | Electroluminescent compounds with high efficiency and organic light-emitting diode using the same |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9153790B2 (en) | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
US20120187383A1 (en) * | 2010-08-11 | 2012-07-26 | E.I. Du Pont De Nemours And Company | Electroactive compound and composition and electronic device made with the composition |
JP6359256B2 (en) * | 2013-09-25 | 2018-07-18 | 出光興産株式会社 | ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE |
WO2015089028A1 (en) * | 2013-12-11 | 2015-06-18 | E. I. Du Pont De Nemours And Company | Photoactive compositions for electronic applications |
US9224955B1 (en) * | 2014-10-31 | 2015-12-29 | Feng-wen Yen | Purifying method for organic optoelectronic material |
KR102641909B1 (en) * | 2018-12-10 | 2024-02-27 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
CN114853556B (en) * | 2022-06-14 | 2023-08-29 | 绍兴文理学院 | New synthesis method of 5H-dibenzo [ a, d ] cycloheptene skeleton |
Citations (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0681019A2 (en) | 1994-04-26 | 1995-11-08 | TDK Corporation | Phenylanthracene derivative and organic EL element |
US5707747A (en) | 1993-11-01 | 1998-01-13 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
US5929194A (en) | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
US5962631A (en) | 1995-07-28 | 1999-10-05 | The Dow Chemical Company | 2, 7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
JP2000186066A (en) | 1998-12-22 | 2000-07-04 | Minolta Co Ltd | New amino compound, its production and use thereof |
WO2000053565A1 (en) | 1999-03-11 | 2000-09-14 | Mobil Oil Corporation | Process for preparing organic carbonates |
WO2000070655A2 (en) | 1999-05-13 | 2000-11-23 | The Trustees Of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
WO2001041512A1 (en) | 1999-12-01 | 2001-06-07 | The Trustees Of Princeton University | Complexes of form l2mx as phosphorescent dopants for organic leds |
JP2001226331A (en) | 2000-02-14 | 2001-08-21 | Mitsui Chemicals Inc | Amine compound and organic electroluminescent element containing the compound |
US20010026878A1 (en) | 1997-05-21 | 2001-10-04 | Woo Edmund P. | Fluorene-containing polymers and electroluminescent devices therefrom |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
WO2003008424A1 (en) | 2001-07-18 | 2003-01-30 | E.I. Du Pont De Nemours And Company | Luminescent lanthanide complexes with imine ligands and devices made with such complexes |
WO2003040257A1 (en) | 2001-11-07 | 2003-05-15 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
WO2003063555A1 (en) | 2001-12-26 | 2003-07-31 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
JP2003238501A (en) | 2002-02-18 | 2003-08-27 | Idemitsu Kosan Co Ltd | Aromatic oligoamine derivative and organic electroluminescent element containing the same |
US20030168970A1 (en) * | 2000-11-24 | 2003-09-11 | Tsuyoshi Tominaga | Luminescent element material and luminescent element comprising the same |
WO2003091688A2 (en) | 2001-07-05 | 2003-11-06 | E.I. Du Pont De Nemours And Company | Photoactive lanthanide complexes with phosphine oxides, phosphine oxide-sulfides, pyridine n-oxides, and phosphine oxide-pyridine n-oxides, and devices made with such complexes |
US20030224205A1 (en) | 2002-04-19 | 2003-12-04 | 3M Innovative Properties Company | Electroluminescent materials and methods of manufacture and use |
US6670645B2 (en) | 2000-06-30 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
US20040004433A1 (en) | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US20040038459A1 (en) | 2000-11-28 | 2004-02-26 | Brown Beverley Anne | Field effect transistors and materials and methods for their manufacture |
WO2004016710A1 (en) | 2002-08-15 | 2004-02-26 | E.I. Du Pont De Nemours And Company | Compounds comprising phosphorus-containing metal complexes |
US20040102577A1 (en) | 2002-09-24 | 2004-05-27 | Che-Hsiung Hsu | Water dispersible polythiophenes made with polymeric acid colloids |
US20040127637A1 (en) | 2002-09-24 | 2004-07-01 | Che-Hsiung Hsu | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
US20040263067A1 (en) | 2003-06-27 | 2004-12-30 | Canon Kabushiki Kaisha | Anthryl derivative group substituted compound, and organic luminescent device making use of same |
US20050205860A1 (en) | 2004-03-17 | 2005-09-22 | Che-Hsiung Hsu | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
EP1624500A1 (en) | 2004-08-05 | 2006-02-08 | Novaled GmbH | Spiro bifluorene compounds as organic semiconductor matrix materials |
US20060033421A1 (en) | 2002-07-19 | 2006-02-16 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and organic light emitting medium |
US7023013B2 (en) | 2004-06-16 | 2006-04-04 | Eastman Kodak Company | Array of light-emitting OLED microcavity pixels |
WO2006063852A1 (en) | 2004-12-18 | 2006-06-22 | Merck Patent Gmbh | Electroluminescent polymers and use thereof |
US20060216411A1 (en) | 2003-09-17 | 2006-09-28 | Toppan Printing Co., Ltd | Electroluminescent device |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
US20070096082A1 (en) | 2003-11-17 | 2007-05-03 | Scott Gaynor | Crosslinkable arylamine compounds and conjugated oligomers or polymers based thereon |
WO2007065678A1 (en) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Novel materials for organic electroluminiescent devices |
JP2007182432A (en) | 2005-12-08 | 2007-07-19 | Mitsubishi Chemicals Corp | Organic compound, electric charge-transporting material, electric charge-transporting material composition and organic electric field light-emitting element |
US20070228364A1 (en) | 2005-12-27 | 2007-10-04 | Radu Nora S | Compositions comprising novel copolymers and electronic devices made with such compositions |
US20070285009A1 (en) * | 2006-04-03 | 2007-12-13 | Idemitsu Kosan Co., Ltd. | Bisanthracene derivative and organic electroluminescence device using the same |
US20080071049A1 (en) | 2006-08-24 | 2008-03-20 | Radu Nora S | Hole transport polymers |
US20080097076A1 (en) | 2006-08-24 | 2008-04-24 | Radu Nora S | Hole transport polymers |
US20080102312A1 (en) | 2004-04-26 | 2008-05-01 | Merck Patent Gmbh | Electroluminescent Polymers Containing Planar Arylamine Units, the Preparation and Use Thereof |
US20080138655A1 (en) | 2006-11-13 | 2008-06-12 | Daniel David Lecloux | Organic electronic device |
US20090051281A1 (en) | 2006-02-15 | 2009-02-26 | Idemitsu Kosan Co., Ltd | Polymeric compound for organic electroluminescence and method for production thereof |
US7540978B2 (en) | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
US20090184635A1 (en) | 2006-07-25 | 2009-07-23 | Merck Patent Gmbh | Polymer blends and their use in organic light emitting devices |
US20090206748A1 (en) | 2005-09-14 | 2009-08-20 | Idemitsu Kosan Co., Ltd. | Method for producing aromatic compound and aromatic compound |
US7745017B2 (en) | 2004-06-28 | 2010-06-29 | Fujifilm Corporation | Organic electroluminescent device and method for producing the same |
US7887933B2 (en) | 2001-07-09 | 2011-02-15 | Merck Patent Gmbh | Electroluminescent materials and devices |
US8063399B2 (en) | 2007-11-19 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Electroactive materials |
Family Cites Families (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3816969B2 (en) * | 1994-04-26 | 2006-08-30 | Tdk株式会社 | Organic EL device |
JP3586906B2 (en) | 1994-12-14 | 2004-11-10 | 凸版印刷株式会社 | Method for manufacturing transparent conductive film |
AU3715997A (en) | 1996-06-12 | 1998-01-07 | Trustees Of Princeton University, The | Plasma treatment of conductive layers |
JP3835917B2 (en) | 1998-02-04 | 2006-10-18 | 三井化学株式会社 | Organic electroluminescence device |
JPH11338172A (en) | 1998-05-27 | 1999-12-10 | Chisso Corp | Naphthalene derivative and organic electroluminescent element using same |
JP2000068073A (en) | 1998-08-27 | 2000-03-03 | Futaba Corp | Organic electroluminescent element and its manufacture |
CN100382354C (en) | 1999-02-15 | 2008-04-16 | 出光兴产株式会社 | Organic electroluminescent element and method for manufacturing the same |
JP4220624B2 (en) | 1999-07-30 | 2009-02-04 | 三井化学株式会社 | Amine compounds |
CN1226250C (en) * | 2000-03-29 | 2005-11-09 | 出光兴产株式会社 | Anthracene derivative and electroluminescent device using the same |
GB0031634D0 (en) | 2000-12-23 | 2001-02-07 | Johnson Matthey Plc | Organic materials |
JP4066619B2 (en) | 2001-07-13 | 2008-03-26 | 三菱化学株式会社 | Binaphthyl compound, method for producing the same, and organic electroluminescent device |
TW588105B (en) | 2001-07-19 | 2004-05-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light-emitting device using the same |
JP2003282274A (en) | 2002-03-25 | 2003-10-03 | Dainippon Printing Co Ltd | Manufacturing method for el electrode |
JP3988539B2 (en) | 2002-06-04 | 2007-10-10 | 三菱化学株式会社 | Organic electroluminescence device |
JP2004107292A (en) | 2002-09-20 | 2004-04-08 | Tosoh Corp | New binaphthalene derivative and method for producing the same |
GB0226010D0 (en) | 2002-11-08 | 2002-12-18 | Cambridge Display Tech Ltd | Polymers for use in organic electroluminescent devices |
US6872475B2 (en) | 2002-12-03 | 2005-03-29 | Canon Kabushiki Kaisha | Binaphthalene derivatives for organic electro-luminescent devices |
JP2004224766A (en) * | 2003-01-27 | 2004-08-12 | Idemitsu Kosan Co Ltd | Bisanthracene derivative, material for forming luminescent coating film and organic electroluminescent element |
EP1596637A4 (en) | 2003-02-20 | 2007-09-05 | Fujifilm Corp | Organic el element and production method therefor |
US6953705B2 (en) | 2003-07-22 | 2005-10-11 | E. I. Du Pont De Nemours And Company | Process for removing an organic layer during fabrication of an organic electronic device |
JP3915757B2 (en) | 2003-08-14 | 2007-05-16 | ソニーケミカル&インフォメーションデバイス株式会社 | Electroluminescent polymer, organic EL device and display device |
JP2005063892A (en) | 2003-08-19 | 2005-03-10 | Seiko Epson Corp | Organic electroluminescent device, manufacturing method of organic electroluminescent el device, and electronic equipment |
KR101283742B1 (en) | 2003-11-14 | 2013-07-08 | 스미또모 가가꾸 가부시키가이샤 | Polymers of Halogenated Bisdiarylaminopolycyclic Aromatic Compounds |
CN1882632B (en) | 2003-11-17 | 2012-04-04 | 住友化学株式会社 | Crosslinkable substituted fluorene compounds and conjugated oligomers or polymers based thereon |
KR20050073233A (en) | 2004-01-09 | 2005-07-13 | 삼성코닝 주식회사 | Manufacturing method of indium tin oxide thin film |
US7365230B2 (en) | 2004-02-20 | 2008-04-29 | E.I. Du Pont De Nemours And Company | Cross-linkable polymers and electronic devices made with such polymers |
JP2005243300A (en) | 2004-02-24 | 2005-09-08 | Sanyo Electric Co Ltd | Organic electroluminescent element and manufacturing method of the same |
US20070181874A1 (en) | 2004-12-30 | 2007-08-09 | Shiva Prakash | Charge transport layers and organic electron devices comprising same |
EP1847521A4 (en) | 2005-02-10 | 2009-05-27 | Idemitsu Kosan Co | Bisanthracene derivative and organic electroluminescent device using same |
JP4832017B2 (en) | 2005-04-25 | 2011-12-07 | ケミプロ化成株式会社 | Binaphthyl derivative, host material comprising the same, hole transport material, and organic EL device using the same |
EP1933603A1 (en) | 2005-09-12 | 2008-06-18 | Idemitsu Kosan Co., Ltd. | Conductive laminate and organic el device |
JP4991737B2 (en) * | 2005-10-21 | 2012-08-01 | エルジー・ケム・リミテッド | Novel binaphthalene derivative, method for producing the same, and organic electronic device using the same |
CN101374789B (en) * | 2006-01-27 | 2014-04-30 | Lg化学株式会社 | New anthracene derivatives, preparation method thereof and organic light emitting diode using the same |
KR100765728B1 (en) | 2006-03-31 | 2007-10-11 | 성균관대학교산학협력단 | Surface treatment method of ito using oxygen plasma and thermal treatment and oled device using the same method |
EP2162424A1 (en) | 2007-06-01 | 2010-03-17 | E. I. Du Pont de Nemours and Company | Hole transport materials |
US8343381B1 (en) | 2008-05-16 | 2013-01-01 | E I Du Pont De Nemours And Company | Hole transport composition |
EP2353196A4 (en) | 2008-12-01 | 2012-07-04 | Du Pont | Anode for an organic electronic device |
EP2352802A4 (en) | 2008-12-01 | 2012-10-31 | Du Pont | Electroactive materials |
JP2012510474A (en) | 2008-12-01 | 2012-05-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Electroactive materials |
WO2010065700A2 (en) | 2008-12-04 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Electroactive materials |
-
2008
- 2008-05-29 EP EP08756397A patent/EP2176374A2/en not_active Withdrawn
- 2008-05-29 KR KR1020147035855A patent/KR101589864B1/en active IP Right Grant
- 2008-05-29 KR KR1020097027391A patent/KR101644193B1/en active IP Right Grant
- 2008-05-29 CN CN2008800171262A patent/CN101689467B/en not_active Expired - Fee Related
- 2008-05-29 CN CN2012100444357A patent/CN102617266A/en active Pending
- 2008-05-29 WO PCT/US2008/065016 patent/WO2008150822A2/en active Application Filing
- 2008-05-29 CN CN2012100444198A patent/CN102603459A/en active Pending
- 2008-05-29 EP EP12166882A patent/EP2487219A1/en not_active Withdrawn
- 2008-05-29 JP JP2010510475A patent/JP5453249B2/en active Active
- 2008-05-30 TW TW097120371A patent/TW200906764A/en unknown
- 2008-05-30 US US12/129,785 patent/US8241762B2/en active Active
-
2012
- 2012-07-12 US US13/547,899 patent/US8460802B2/en not_active Expired - Fee Related
Patent Citations (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5707747A (en) | 1993-11-01 | 1998-01-13 | Hodogaya Chemical Co., Ltd. | Amine compound and electro-luminescence device comprising same |
EP0681019A2 (en) | 1994-04-26 | 1995-11-08 | TDK Corporation | Phenylanthracene derivative and organic EL element |
US5962631A (en) | 1995-07-28 | 1999-10-05 | The Dow Chemical Company | 2, 7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
US5929194A (en) | 1996-02-23 | 1999-07-27 | The Dow Chemical Company | Crosslinkable or chain extendable polyarylpolyamines and films thereof |
US20010026878A1 (en) | 1997-05-21 | 2001-10-04 | Woo Edmund P. | Fluorene-containing polymers and electroluminescent devices therefrom |
US6303238B1 (en) | 1997-12-01 | 2001-10-16 | The Trustees Of Princeton University | OLEDs doped with phosphorescent compounds |
JP2000186066A (en) | 1998-12-22 | 2000-07-04 | Minolta Co Ltd | New amino compound, its production and use thereof |
WO2000053565A1 (en) | 1999-03-11 | 2000-09-14 | Mobil Oil Corporation | Process for preparing organic carbonates |
WO2000070655A2 (en) | 1999-05-13 | 2000-11-23 | The Trustees Of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
WO2001041512A1 (en) | 1999-12-01 | 2001-06-07 | The Trustees Of Princeton University | Complexes of form l2mx as phosphorescent dopants for organic leds |
JP2001226331A (en) | 2000-02-14 | 2001-08-21 | Mitsui Chemicals Inc | Amine compound and organic electroluminescent element containing the compound |
US6670645B2 (en) | 2000-06-30 | 2003-12-30 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
US20030168970A1 (en) * | 2000-11-24 | 2003-09-11 | Tsuyoshi Tominaga | Luminescent element material and luminescent element comprising the same |
US20040038459A1 (en) | 2000-11-28 | 2004-02-26 | Brown Beverley Anne | Field effect transistors and materials and methods for their manufacture |
WO2003091688A2 (en) | 2001-07-05 | 2003-11-06 | E.I. Du Pont De Nemours And Company | Photoactive lanthanide complexes with phosphine oxides, phosphine oxide-sulfides, pyridine n-oxides, and phosphine oxide-pyridine n-oxides, and devices made with such complexes |
US7887933B2 (en) | 2001-07-09 | 2011-02-15 | Merck Patent Gmbh | Electroluminescent materials and devices |
WO2003008424A1 (en) | 2001-07-18 | 2003-01-30 | E.I. Du Pont De Nemours And Company | Luminescent lanthanide complexes with imine ligands and devices made with such complexes |
WO2003040257A1 (en) | 2001-11-07 | 2003-05-15 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
WO2003063555A1 (en) | 2001-12-26 | 2003-07-31 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
JP2003238501A (en) | 2002-02-18 | 2003-08-27 | Idemitsu Kosan Co Ltd | Aromatic oligoamine derivative and organic electroluminescent element containing the same |
US20030224205A1 (en) | 2002-04-19 | 2003-12-04 | 3M Innovative Properties Company | Electroluminescent materials and methods of manufacture and use |
US20070079927A1 (en) | 2002-06-26 | 2007-04-12 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US20040004433A1 (en) | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US20050191776A1 (en) | 2002-06-26 | 2005-09-01 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
US20060033421A1 (en) | 2002-07-19 | 2006-02-16 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and organic light emitting medium |
WO2004016710A1 (en) | 2002-08-15 | 2004-02-26 | E.I. Du Pont De Nemours And Company | Compounds comprising phosphorus-containing metal complexes |
US7189989B2 (en) | 2002-08-22 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Light emitting element |
US20040127637A1 (en) | 2002-09-24 | 2004-07-01 | Che-Hsiung Hsu | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
US20040102577A1 (en) | 2002-09-24 | 2004-05-27 | Che-Hsiung Hsu | Water dispersible polythiophenes made with polymeric acid colloids |
US20040263067A1 (en) | 2003-06-27 | 2004-12-30 | Canon Kabushiki Kaisha | Anthryl derivative group substituted compound, and organic luminescent device making use of same |
US20060216411A1 (en) | 2003-09-17 | 2006-09-28 | Toppan Printing Co., Ltd | Electroluminescent device |
US20070096082A1 (en) | 2003-11-17 | 2007-05-03 | Scott Gaynor | Crosslinkable arylamine compounds and conjugated oligomers or polymers based thereon |
US20050205860A1 (en) | 2004-03-17 | 2005-09-22 | Che-Hsiung Hsu | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
US20080102312A1 (en) | 2004-04-26 | 2008-05-01 | Merck Patent Gmbh | Electroluminescent Polymers Containing Planar Arylamine Units, the Preparation and Use Thereof |
US7023013B2 (en) | 2004-06-16 | 2006-04-04 | Eastman Kodak Company | Array of light-emitting OLED microcavity pixels |
US7745017B2 (en) | 2004-06-28 | 2010-06-29 | Fujifilm Corporation | Organic electroluminescent device and method for producing the same |
EP1624500A1 (en) | 2004-08-05 | 2006-02-08 | Novaled GmbH | Spiro bifluorene compounds as organic semiconductor matrix materials |
US7540978B2 (en) | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
US20100108989A1 (en) | 2004-12-18 | 2010-05-06 | Merck Patent Gmbh | Electroluminescent polymers and use thereof |
WO2006063852A1 (en) | 2004-12-18 | 2006-06-22 | Merck Patent Gmbh | Electroluminescent polymers and use thereof |
US20090206748A1 (en) | 2005-09-14 | 2009-08-20 | Idemitsu Kosan Co., Ltd. | Method for producing aromatic compound and aromatic compound |
JP2007182432A (en) | 2005-12-08 | 2007-07-19 | Mitsubishi Chemicals Corp | Organic compound, electric charge-transporting material, electric charge-transporting material composition and organic electric field light-emitting element |
WO2007065678A1 (en) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Novel materials for organic electroluminiescent devices |
US20070228364A1 (en) | 2005-12-27 | 2007-10-04 | Radu Nora S | Compositions comprising novel copolymers and electronic devices made with such compositions |
US20090051281A1 (en) | 2006-02-15 | 2009-02-26 | Idemitsu Kosan Co., Ltd | Polymeric compound for organic electroluminescence and method for production thereof |
US20070285009A1 (en) * | 2006-04-03 | 2007-12-13 | Idemitsu Kosan Co., Ltd. | Bisanthracene derivative and organic electroluminescence device using the same |
US20090184635A1 (en) | 2006-07-25 | 2009-07-23 | Merck Patent Gmbh | Polymer blends and their use in organic light emitting devices |
US20080097076A1 (en) | 2006-08-24 | 2008-04-24 | Radu Nora S | Hole transport polymers |
US20080071049A1 (en) | 2006-08-24 | 2008-03-20 | Radu Nora S | Hole transport polymers |
US20080138655A1 (en) | 2006-11-13 | 2008-06-12 | Daniel David Lecloux | Organic electronic device |
US8063399B2 (en) | 2007-11-19 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Electroactive materials |
Non-Patent Citations (10)
Title |
---|
Colon et al-High Molecular Weight Aromatic Polymers by Nickel Coupling of Aryl Polychlorides; Journal of Polymer Science, Part A, Polymer Chemistry Edition, 1990, vol. 28: 367. |
Colon et al—High Molecular Weight Aromatic Polymers by Nickel Coupling of Aryl Polychlorides; Journal of Polymer Science, Part A, Polymer Chemistry Edition, 1990, vol. 28: 367. |
CRC Handbook of Chemistry and Physics, 81st Edition, 2000, (Book Not Included). |
Eaton et al-Dihedral Angle of Biphenyl in Solution and the Molecular Force Field; J. Chem. Soc. Faraday Trans. 2, 1973, 60 pp. 1601-1608. |
Eaton et al—Dihedral Angle of Biphenyl in Solution and the Molecular Force Field; J. Chem. Soc. Faraday Trans. 2, 1973, 60 pp. 1601-1608. |
Gustafsson et al., Nature, 1992, vol. 357:477-479. |
John Markus, Photoconductive Cell, Electronics and Nucleonics Dictionary, 1966, pp. 470, 471 & 476, Mc-Graw-Hill. |
Wang, Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition, 1996, vol. 18:837-860. |
Written Opinion of the International Searching Authority, WO 2008/150822, PCT/US2008/065016, PCT counterpart of the present application, Dec. 1, 2009. |
Written Opinion of the International Searching Authority, WO 2008PCT/US2008/065016, PCT Counterpart of the Present Application, Dec. 1, 2009. |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US20110152587A1 (en) * | 2007-04-13 | 2011-06-23 | Hyo Nim Shin | Electroluminescent compounds with high efficiency and organic light-emitting diode using the same |
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CN102603459A (en) | 2012-07-25 |
WO2008150822A3 (en) | 2009-02-05 |
CN101689467A (en) | 2010-03-31 |
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TW200906764A (en) | 2009-02-16 |
JP5453249B2 (en) | 2014-03-26 |
KR101589864B1 (en) | 2016-01-29 |
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CN101689467B (en) | 2012-10-03 |
WO2008150822A2 (en) | 2008-12-11 |
EP2176374A2 (en) | 2010-04-21 |
US20080297040A1 (en) | 2008-12-04 |
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KR20150016582A (en) | 2015-02-12 |
US8460802B2 (en) | 2013-06-11 |
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JP2010529030A (en) | 2010-08-26 |
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